Tetrahedron Letters

A kinetic study of the mechanism of esterification of 1-arylethanols in trifluoroacetic acid

CJ Gillen, AC Knipe, WE Watts

Index: Gillen, Ciaran J.; Knipe, Anthony C.; Watts, William E. Tetrahedron Letters, 1981 , vol. 22, p. 597 - 600

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Abstract

Abstract Aryl substituent effects upon the rate constants for the esterification of a series of 1- arylethanols in trifluoroacetic acid are in accordance with a reverse A AL 1 mechanism, for which the Hammett reaction constant ϱ=− 3.69 has been determined by correlation with σ+ substituent constants. The rates of reaction are ca. 50-fold faster than those for corresponding benzyl alcohols which bear an electron-donating aryl substituent and ...